Modern Projects and Experiments in Organic Chemistry : Miniscale and Williamson Microscale

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The Manuals Modern Projects and Experiments in Organic Chemistryhelps instructors turn their organic chemistry laboratories into places of discovery and critical thinking. In addition to traditional experiments, the manual offers a variety of inquiry-based experiments and multi-week projects, giving students a better understanding of how lab work is actually accomplished. Instead of simply following directions, students learn how to investigate the experimental process itself. The Program Modern Projects and Experiments in Organic Chemistryis designed to provide the utmost in quality content, student accessibility, and instructor flexibility. The project consists of: 1) A laboratory manual in two versions: miniscale and standard-taper microscale equipment (0-7167-9779-8) miniscale and Williamson microscale equipment (0-7167-3921-6) 2) Custom publishing option.All experiments are available through Freeman's custom publishing service at http://custompub.whfreeman.com. Instructors can use this service to create their own customized lab manual, even including their own material. 3)Techniques in Organic Chemistry. This concise yet comprehensive companion volume provides students with detailed descriptions of important techniques.

Preface

xi

PART 1 EXPERIMENTS

1

(236)

Extraction of Caffeine from Tea

3

(6)

Purification and Thin-Layer Chromatographic Analysis of Caffeine

9

(6)

Optional Experiment: Evaluating TLC Parameters

13

(2)

Synthesis of Ethanol by Fermentation of Sucrose

15

(4)

Synthesis of Salicylic Acid

19

(8)

Analgesics and Synthesis of Aspirin

27

(10)

Synthesis of Acetylsalicylic Acid

29

(4)

Thin-Layer Chromatographic Analysis of Analgesics

33

(4)

Isolation of Essential Oils from Plants

37

(10)

(S)-(+)-Carvone from Caraway Seeds

40

(4)

Isolation of (R)-(+)-Limonene from Orange Peels

44

(3)

Computational Chemistry

47

(10)

Radical Halogenation Reactions

57

(10)

Radical Chlorination Reactions

59

(4)

Optional Experiment: Additional Substrates

62

(1)

Optional Computational Chemistry Experiment

62

(1)

Photobromination of 1,2-Diphenylethane

63

(4)

Nucleophilic Substitution Reactions

67

(10)

SN1/SN2 Reactivity of Alkyl Halides

70

(2)

Synthesis and Identification of Alkyl Bromides from Unknown Alcohols

72

(5)

E2 Elimination of 2-Bromoheptane: Influence of the Base

77

(6)

Optional Computational Chemistry Experiment

80

(3)

Dehydration of Alcohols

83

(10)

Acid-Catalyzed Dehydration of 2-Methyl-2-butanol

86

(3)

Optional Experiment: Qualitative Tests for Alkenes

88

(1)

Acid-Catalyzed Dehydration of 3-Methylcyclohexanol

89

(4)

Optional Experiment: Qualitative Tests for Alkenes

91

(2)

Synthesis of Esters from Alcohols

93

(14)

Synthesis of Isopentyl Acetate

95

(5)

Optional Experiment: Synthesis and Identification of an Ester from an Unknown Alcohol and Acetic Acid

98

(2)

Synthesis of Benzocaine

100

(3)

Determination of the Equilibrium Constant for an Esterification Reaction

103

(4)

Green Chemistry: Oxidation of Cyclohexanol Using Sodium Hypochlorite

107

(8)

Oxidation of Cinnamyl Alcohol Using Pyridinium Chlorochromate

115

(6)

Grignard Syntheses

121

(12)

Synthesis of Phenylmagnesium Bromide for Use as a Synthetic Intermediate